Divergent reactions on racemic mixtures
Laura C Miller1, Richmond Sarpong
1Department of Chemistry, Princeton University, Princeton, NJ 08544, USA.
This review explores using divergent reactions on racemic mixtures to create enantioenriched products. This underutilized strategy employs a single chiral reagent to yield two distinct, enantiomerically enriched compounds from each enantiomer of the starting material.
Area of Science:
- Organic Chemistry
- Asymmetric Synthesis
Background:
- Enantioenriched products are vital in modern organic synthesis.
- Developing efficient methods for their synthesis remains a key challenge.
Purpose of the Study:
- To review the underutilized strategy of divergent reactions on racemic mixtures.
- To highlight the potential for generating enantioenriched products through this approach.
Main Methods:
- Discussing divergent reactions on racemic starting materials.
- Utilizing a single chiral reagent to react with each enantiomer separately.
- Focusing on stereodivergent, regiodivergent, and structurally divergent reactions.
Main Results:
- Each enantiomer of the racemic mixture yields a distinct, separable product.
- The resulting products are enantioenriched, offering a route to chiral compounds.
- Demonstrates the versatility of the divergent reaction strategy.
Conclusions:
- Divergent reactions on racemic mixtures offer an efficient and underutilized pathway to enantioenriched compounds.
- This strategy provides access to multiple, separable, and enantiomerically enriched products.
- Highlights the importance of exploring novel synthetic methodologies.
More Related Videos
10:12Retropinacol/Cross-pinacol Coupling Reactions - A Catalytic Access to 1,2-Unsymmetrical Diols
Published on: April 4, 2014
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Racemic Mixtures and the Resolution of Enantiomers
SN1 Reaction: Stereochemistry
In the first step of an SN1 reaction, the bond between the electrophilic carbon and the leaving group ionizes to generate the carbocation intermediate. The second step of the mechanism is the nucleophilic attack.
In the formed carbocation, the positively charged carbon is sp2 hybridized with a trigonal planar geometry. As all the three substituents lie on the same plane, a plane of symmetry for the...
Regioselectivity of Electrophilic Additions-Peroxide Effect
Radical Halogenation: Stereochemistry
Halogenation to form a new chiral center:
Preparation of Alcohols via Substitution Reactions
Alcohols can be synthesized from alkyl halides via nucleophilic substitution reactions. The highly polar carbon-halogen bond in the substrate makes halide a good leaving group. The hydroxide ion or water can act as a nucleophile to take the place of halide and form an alcohol. The substitution reactions occur via two different reaction pathways, SN1 or SN2, depending on the nature of carbon attached to the halide.
Primary alcohols are synthesized from primary alkyl halides, and the...
Prochirality
